THE NEW RULES OF 21ST-CENTURY STYLE

September 21, 2014

Fifty-eight observations, exhortations, and hard-won insights into how to dress now.
By the Fashion Editors of Esquire

1: Make it custom. Because in this day and age, anything and everything in your closet can be customized. Options range from computerized made-to-measure (i.e., those nifty Web sites that ask you to measure your own shoulders) to full-blown bespoke (i.e., rendered with you in mind from the first stitch). The happiest of mediums comes from Prada: Its made-to-measure program for suits, shirts, et al. is overseen by its team of tailors and craftsmen, who customize the fits and finishes to your liking. In the world according to Prada, the possibilities are practically endless.

2: It is only when a man doesn’t have much to say (parole hearings, pool parties, the priesthood) that his choice of clothing doesn’t mean much. With options come obligations, and the more options you’ve got, the more your choices matter.

3: That hat doesn’t look as good as he thinks it does.

4: Appropriate is overrated. Rakish is underrated. On-trend is a compound adjective that one must never utter aloud but is perfectly acceptable to keep in mind.

9: The best-dressed group of men on television right now: late-night hosts (see above). The worst dressed: the walking dead on The Walking Dead.

10: The upper-left-hand quadrant of your torso is your sartorial sandbox. Lapel pins, pocket squares, et al. are all toys for the tinkering.

11: The coworker who occasionally changes into a tuxedo before leaving for the evening is not someone you want to have as an enemy.

12: A stiff wind, an arctic clime, ice falling from the sky: such are the conditions that necessitate the looping/knotting/folding of a long fringed scarf around one’s neck.

13: Was an overactive office air conditioner or an inflated sense of self among the conditions that necessitate the looping/knotting/folding of a long fringed scarf around one’s neck? It was not.

14: Cell phone: not to be seen nor heard nor brandished mid-meeting to check for incoming texts.

15: Yes, you still have to wear a cummerbund.

16: Small men don’t wear big coats.

17: Big men shouldn’t wear small coats.

18: You look 43 percent less virile in that selfie.

19: No selfies.

20: Hipsters are the locusts of personal style. They appropriate looks and sensibilities, eradicate all credibility, and then move on, leaving everything behind them a little worse for their having worn them. See: elbow patches, chunky eyewear, monk-straps, fedoras: The list is long and tragic.

21: V-neck collars should not dip below the top of your sternum. Leave the bearing of cleavage to the ladies of The View.

22: The tote bag is the new messenger bag. The messenger bag is the new backpack. The backpack is the new fanny pack.